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Nov 7 - Nov 9
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Nov 28 - Nov 30
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Dec 26 - Dec 28

B&B in Winchester

Exterior
Glen Gordon Manor
Glen Gordon Manor
3.5 star property
9.8 out of 10, Exceptional, (91)
"Such a beautiful property. Dinner and breakfast was scrumptious. It is perfect :DC getaway. Highly recommended. "
United States
Nitin
$249 nightly
The price is $272
Nov 5 - Nov 6
Total with taxes and fees
Glen Gordon Manor
Reception
Loudoun Valley Manor
Loudoun Valley Manor
3.0 star property
9.6 out of 10, Exceptional, (272)
"Just a beautiful, serene property hosted and run by a lovely woman- Olga. Breakfast was freshly made to order and our room was very nicely appointed and super clean. Beautiful place overall with many wineries nearby. "
United States
Janet
$140 nightly
The price is $160
Nov 3 - Nov 4
Total with taxes and fees
Loudoun Valley Manor
Free daily full breakfast
Inn at Evergreen
Inn at Evergreen
3.5 star property
9.4 out of 10, Exceptional, (131)
"This is a lovely property. We were lucky to have a suite - so restful and quiet. The breakfast across the street at the golf club was delicious. There is a lot to do in the area if you're not into golf."
United States
Valerie
$206 nightly
The price is $235
Nov 12 - Nov 13
Total with taxes and fees
Inn at Evergreen
Property amenity
Hillbrook Inn
Hillbrook Inn
4.0 star property
8.6 out of 10, Excellent, (670)
"We had an amazing day at the Hillbrook Inn. I recommend this to anybody who would like a quiet serene stay. Staff is wonderful and the food is amazing. "
United States
Karley
$195 nightly
The price is $216
Nov 16 - Nov 17
Total with taxes and fees
Hillbrook Inn
Family House, Multiple Beds, Balcony, Garden Area | Balcony
Hopkins Ordinary Bed Breakfast and Ale Works
Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
10.0 out of 10, Exceptional, (31)
"The Inn was on a lovely property near a river walk. An amazing ale house is also on the property. Very quaint and comfortable. Games, books and a front porch swing were provided. Our hosts were accommodating and friendly. The Breakfests were exceptional with delightful farm fresh eggs and produce. Overall it was a very relaxing and fun getaway. A side note that Sperryville is a weekend town there was not much to do during the week. "
United States
Sherry
$287 nightly
The price is $313
Nov 17 - Nov 18
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
Garden
Stone Manor Boutique Inn
Stone Manor Boutique Inn
3.5 star property
9.6 out of 10, Exceptional, (95)
"The experience was very good, will return in the future. The breakfast was excellent. "
United States
Marvin
$242 nightly
The price is $275
Nov 3 - Nov 4
Total with taxes and fees
Stone Manor Boutique Inn
Exterior
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
2.0 star property
10.0 out of 10, Exceptional, (1)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
$2,016 nightly
The price is $2,387
Nov 9 - Nov 10
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Property entrance
The Inn at Grass Roots Hill
The Inn at Grass Roots Hill
3.0 star property
10.0 out of 10, Exceptional, (2)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
$459 nightly
The price is $523
Nov 3 - Nov 4
Total with taxes and fees
The Inn at Grass Roots Hill
Garden
Cantuta Inn
Cantuta Inn
3.0 star property
9.0 out of 10, Wonderful, (73)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
United States
Aleta
$165 nightly
The price is $185
Nov 9 - Nov 10
Total with taxes and fees
Cantuta Inn
Interior detail
Gay Street Inn
Gay Street Inn
3.5 star property
10.0 out of 10, Exceptional, (34)
"The Gay street Inn was fantastic. Very very friendly service and the breakfast was amazing. "
United States
Amy
$359 nightly
The price is $387
Nov 6 - Nov 7
Total with taxes and fees
Gay Street Inn
Dining
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
10.0 out of 10, Exceptional, (3)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
United States
Daniel F.
$256 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Outdoor pool
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
9.8 out of 10, Exceptional, (36)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
United States
Tatiana
$428 nightly
The price is $488
Nov 3 - Nov 4
Total with taxes and fees
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Pool
The Van Gogh Room in Villa
The Van Gogh Room in Villa
9.0 out of 10, Wonderful, (67)
"Nice rooms, beautiful property, accommodating host. The pool and gardens are serene and relaxing. Easy drive to many local restaurants, winery’s, breweries…. Close to the AT for those looking to recovery from hiking "
United States
Darla B.
$371 nightly
The price is $423
Nov 3 - Nov 4
Total with taxes and fees
The Van Gogh Room in Villa
Courtyard
The Carriage Inn B&B
The Carriage Inn B&B
3.5 star property
9.6 out of 10, Exceptional, (432)
"Excellent, historic, amazing breakfast and hostess"
United States
David
$124 nightly
The price is $141
Dec 3 - Dec 4
Total with taxes and fees
The Carriage Inn B&B
Dining
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
10.0 out of 10, Exceptional, (3)
"A very nice and charming house. We really enjoyed our stay. I do 2 recommendations. Put a sitting chair in the room and put some surgar with the coffee."
United States
Alan H.
$282 nightly
The price is $313
Nov 9 - Nov 10
Total with taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Appalachian Suite In Town!- The Grand Castalian Inn B&B
10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
United States
Seth W.
$270 nightly
The price is $299
Nov 3 - Nov 4
Total with taxes and fees
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Dining
50's Drive-In Inside the Grand Castalian Inn B&B
50's Drive-In Inside the Grand Castalian Inn B&B
2.0 star property
$283 nightly
The price is $314
Nov 3 - Nov 4
Total with taxes and fees
50's Drive-In Inside the Grand Castalian Inn B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"The room was very clean and the staff were very accommodating. "
Colleen 1-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,117
Accommodation
33 B&B
Lowest Price
$141
Highest Price
$2,387

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $141 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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